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Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 11
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General Xenobiochemistry

Characterization of glutathione conjugates derived from reactive metabolites of seven silymarin isomers

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Pages 1269-1278 | Received 19 Sep 2018, Accepted 14 Nov 2018, Published online: 07 Jan 2019

References

  • Agarwal R. (2000). Cell signaling and regulators of cell cycle as molecular targets for prostate cancer prevention by dietary agents. Biochem. Pharmacol 60:1051–9.
  • Akiyoshi T, Ito M, Murase S, et al. (2013). Mechanism-based inhibition profiles of erythromycin and clarithromycin with cytochrome P450 3A4 genetic variants. Drug Metab Pharmacokinet 28:411–5.
  • Beckmann-Knopp S, Rietbrock S, Weyhenmeyer R, et al. (2000). Inhibitory effects of silibinin on cytochrome P-450 enzymes in human liver microsomes. Pharmacol Toxicol 86:250–6.
  • Chen J, Peng Y, Zheng J. (2016). Cytochrome P450 mediated bioactivation of saracatinib. Chem Res Toxicol 29:1835–42.
  • Deng JW, Shon JH, Shin HJ, et al. (2008). Effect of silymarin supplement on the pharmacokinetics of rosuvastatin. Pharm Res 25:1807–14.
  • Ekins S, Stresser DM, Williams JA. (2003). In vitro and pharmacophore insights into CYP3A enzymes. Trends Pharmacol Sci 24:161–6.
  • Federico A, Trappoliere M, Tuccillo C, et al. (2006). A new silybin-vitamin E-phospholipid complex improves insulin resistance and liver damage in patients with non-alcoholic fatty liver disease: Preliminary observations. Gut 55:901–2.
  • Flora K, Hahn M, Rosen H, Benner K. (1998). Milk thistle (Silybum marianum) for the therapy of liver disease (see comments). Am J Gastroenterol 93:139–43.
  • Gerhauser C, Klimo K, Heiss E, et al. (2003). Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutat. Res 523-524:163–72.
  • Guo X, Lin D, Li W, et al. (2016). Electrophilicities and protein covalent binding of demethylation metabolites of colchicine. Chem Res Toxicol 29:296–302.
  • Haefeli WE, Carls A. (2014). Drug interactions with phytotherapeutics in oncology. Expert Opin Drug Metab Toxicol 10:359–77.
  • Hutzler JM, Melton RJ, Rumsey JM, et al. (2006). Inhibition of cytochrome P450 3A4 by a pyrimidineimidazole: Evidence for complex heme interactions. Chem Res Toxicol 19:1650–9.
  • Hutzler JM, Melton RJ, Rumsey JM, et al. (2008). Assessment of the metabolism and intrinsic reactivity of a novel catechol metabolite. Chem Res Toxicol 21:1125–33.
  • Ji L, Lu D, Cao J, et al. (2015). Psoralen, a mechanism-based inactivator of CYP2B6. Chem Biol Interact 240:346–52.
  • Kosina P, Maurel P, Ulrichová J, Dvorák Z. (2005). Effect of silybin and its glycosides on the expression of cytochromes P450 1A2 and 3A4 in primary cultures of human hepatocytes. J Biochem Mol Toxicol 19:149–53.
  • Kren V, Walterová D. (2005). Silybin and silymarin-New effects and applications. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 149:29–41.
  • Li HB, Yang YR, Mo ZJ, et al. (2015). Silibinin improves palmitate-induced insulin resistance in C2C12 myotubes by attenuating IRS-1/PI3K/Akt pathway inhibition. Braz J Med Biol Res 48:440–6.
  • Lin G, Tang J, Liu XQ, et al. (2007). Deacetylclivorine: a gender-selective metabolite of clivorine formed in female sprague-dawley rat liver microsomes. Drug Metab. Dispos 35:607–13.
  • Liu YQ, Hong YJ, Zeng S. (2009). Recent advances in metabolism-based drug-drug interactions. Zhejiang Da Xue Xue Bao Yi Xue Ban 38:215–24.
  • Lovelace ES, Maurice N, Miller HW, et al. (2017). Silymarin suppresses basal and stimulus-induced activation, exhaustion, differentiation, and inflammatory markers in primary human immune cells. PLoS One 12:e0171139.
  • Mao X, Hu ZX, Zhou S, et al. (2018). Nitidine chloride is a mechanism-based inactivator of CYP2D6. Drug Metab Dispos 46:1137–45.
  • Mao X, Peng Y, Zheng J. (2015). In vitro and in vivo characterization of reactive intermediates of corynoline. Drug Metab Dispos 43:1491–8.
  • Mooiman KD, Goey AK, Huijbregts TJ, et al. (2014). The in-vitro effect of complementary and alternative medicines on cytochrome P450 2C9 activity. J Pharm Pharmacol 6:1339–46.
  • Nguyen H, Zhang SZ, Morris ME. (2003). Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci 92:250–7.
  • Purchartová K, Engels L, Marhol P, et al. (2013). Enzymatic preparation of silybin phase ii metabolites: sulfation using aryl sulfotransferase from rat liver. Appl Microbiol. Biot 97:10391–8.
  • Sekiguchi N, Kato M, Takada M, et al. (2011). Quantitative prediction of mechanism-based inhibition caused by mibefradil in rats. Drug Metab Dispos 39:1255–62.
  • Siess MH, Leclerc J, Canivenc-Lavier M, et al. (1995). Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol Appl Pharmacol 130:73–8.
  • Singh RP, Agarwal R. (2004). Prostate cancer prevention by silibinin. Curr Cancer Drug Targets 4:1–11.
  • Sridar C, Goosen TC, Kent UM, et al. (2004). Silybin inactivates cytochromes P450 3A4 and 2C9 and inhibits major hepatic glucuronosyltransferases. Drug Metab. Dispos 32:587–94.
  • Tyagi A, Agarwal C, Agarwal R. (2002). Inhibition of retinoblastoma protein (Rb) phosphorylation at serine sites and an increase in Rb-E2F complex formation by silibinin in androgen-dependent human prostate carcinoma LNCaP cells: Role in prostate cancer prevention. Mol Cancer Ther 1:525–32.
  • Venkataramanan R, Ramachandran V, Komoroski BJ, et al. (2000). Milk thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures. Drug Metab Dispos 28:1270–3.
  • Vrba J, Papousková B, Roubalová L, et al. (2018). Metabolism of flavonolignans in human hepatocytes. J Pharm Biomed Anal 152:94–101.
  • Wallace S, Carrier DJ, Beitle RR, et al. (2003). HPLC-UV and LC-MS-MS characterization of silymarin in milk thistle seeds and corresponding products. J. Nutraceuticals Funct. Med. Foods 4:37–48.
  • Wang JY, Chang CC, Chiang CC, et al. (2012). Silibinin suppresses the maintenance of colorectal cancer stem-like cells by inhibiting PP2A/AKT/mTOR pathways. J Cell Biochem 13:1733–43.
  • Wang K, Hu X, Zhang H, Du Q. (2011). Determination of active components in silymarin by UPLC-ESI MS. China J Chinese materia Medica 36:2361–6.
  • Wu JW, Tsai TH. (2007). Effect of silibinin on the pharmacokinetics of pyrazinamide and pyrazinoic acid in rats. Drug Metab. Dispos 35:1603–10.
  • Yao J, Zhi M, Gao X, et al. (2013). Effect and the probable mechanisms of silibinin in regulating insulin resistance in the liver of rats with non-alcoholic fatty liver. Braz J Med Biol Res 46:270–7.
  • Zhang S, Morris ME. (2003). Effect of the flavonoids biochanin A and silymarin on the p-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal caco-2 cells. Pharm. Res 20:1184–91.
  • Zou HM, Zhou C, Sun CJ, et al. (2017). Determination of silymarin in health food by high performance liquid chromatography. Sichuan Da Xue Xue Bao Yi Xue Ban 48:464–70.
  • Zuber R, Modrianský M, Dvořák Z, et al. (2002). Effect of silybin and its congeners on human liver microsomal cytochromeP450 activities. Phytother Res 16:632–8.

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